Embarrassing questions that keep it light

School and work

1. 1.Have you ever missed a cue in a school play, concert or presentation?
2. 2.What were you saying when someone pointed out you were on mute?
3. 3.Have you ever hit reply all when you meant to reply to one person?
4. 4.Have you forgotten your password in front of a room full of people?
5. 5.What question did you mishear in class or a meeting, and what did you answer instead?
6. 6.What did you call a teacher or boss by mistake?
7. 7.Have you walked into the wrong classroom or meeting and sat down before you noticed?
8. 8.What happened the first day at a new school or job that you can laugh about now?
9. 9.Have you ever fallen asleep somewhere you really shouldn't have?
10. 10.What is the oddest true reason you have been late?

Social slips

11. 11.Have you ever waved back at someone who was waving at the person behind you?
12. 12.When did you confidently call someone by the wrong name?
13. 13.What word did you pronounce wrong for years before anyone told you?
14. 14.Have you ever sent a harmless message to the wrong person? What happened?
15. 15.Which outfit looked better in your head than in the photograph?
16. 16.How long did it take you to notice something you were wearing was inside out?
17. 17.Have you tried to open a car that turned out not to be yours?
18. 18.What were you singing when you discovered someone could hear you?
19. 19.Have you gone for a handshake when the other person went for a hug?
20. 20.What did you order without knowing what it was?

Family stories

21. 21.What embarrassing story does your family still tell about you?
22. 22.What did you do as a small child that your parents still bring up?
23. 23.Which childhood photo would you most like to hide, and which would you happily show?
24. 24.What did you believe as a child that turned out to be completely wrong?
25. 25.What did you say in front of a grandparent that you shouldn't have?
26. 26.What happened at a family wedding or holiday that nobody lets you forget?
27. 27.What haircut did a parent give you, or did you give yourself?
28. 28.What did you get caught doing as a teenager that seems funny now?
29. 29.Which of your family's embarrassing stories would you like to hear told by someone else?
30. 30.What embarrassing story about yourself are you happy to have passed down?